(E)-3-(4-Chloro-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

The title compound, C(13)H(9)ClOS, adopts an E configuration with respect to the C=C double bond of the propenone unit. The thienyl and benzene rings are slightly twisted from each other, making a dihedral angle of 6.38 (3)°. An intra-molecular C-H⋯O hydrogen bond generates an S(5) ring motif. A weak inter-molecular C-H⋯O inter-action, a short intra-molecular S⋯O contact [2.932 (2) Å] and two π-π inter-actions between the thienyl and benzene rings are observed. The centroid-centroid distances of the π-π inter-actions are 3.7899 (16) and 3.7891 (16) Å.

Related literature

For related literature on chalcone derivatives, see: Agrinskaya et al. (1999 ▶); Gu, Ji, Patil & Dharmaprakash (2008 ▶); Gu, Ji, Patil, Dharmaprakash & Wang (2008 ▶); Fun et al. (2008 ▶); Patil et al. (2006 ▶); Patil, Dharmaprakash et al. (2007 ▶); Patil, Fun et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9ClOS

M = 248.71

Monoclinic,

a = 5.7023 (3) Å

b = 13.3576 (8) Å

c = 14.7017 (10) Å

β = 96.735 (4)°

V = 1112.09 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 100.0 (1) K

0.45 × 0.13 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.804, T max = 0.942

12436 measured reflections

3238 independent reflections

2546 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.199

S = 1.08

3238 reflections

145 parameters

H-atom parameters constrained

Δρmax = 1.76 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022782/is2316sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022782/is2316Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H9ClOS	F000 = 512
Mr = 248.71	Dx = 1.485 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3595 reflections
a = 5.7023 (3) Å	θ = 2.8–29.8º
b = 13.3576 (8) Å	µ = 0.50 mm−1
c = 14.7017 (10) Å	T = 100.0 (1) K
β = 96.735 (4)º	Needle, colourless
V = 1112.09 (12) Å3	0.45 × 0.13 × 0.12 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3238 independent reflections
Radiation source: fine-focus sealed tube	2546 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 100.0(1) K	θmax = 30.1º
φ and ω scans	θmin = 2.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.804, Tmax = 0.942	k = −16→18
12436 measured reflections	l = −20→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068	H-atom parameters constrained
wR(F2) = 0.199	w = 1/[σ2(Fo2) + (0.0986P)2 + 1.8996P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
3238 reflections	Δρmax = 1.76 e Å−3
145 parameters	Δρmin = −0.49 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.90267 (12)	1.35871 (6)	0.43901 (5)	0.0277 (2)
Cl1	0.00412 (13)	0.64087 (5)	0.29914 (5)	0.0299 (2)
O1	0.9797 (4)	1.14167 (16)	0.44334 (16)	0.0327 (5)
C2	0.4870 (5)	1.4144 (2)	0.3764 (2)	0.0293 (6)
H2A	0.3575	1.4550	0.3579	0.035*
C3	0.4820 (5)	1.3077 (2)	0.37026 (19)	0.0224 (5)
H3A	0.3505	1.2703	0.3476	0.027*
C4	0.7018 (5)	1.2675 (2)	0.40300 (18)	0.0223 (5)
C5	0.7766 (5)	1.1625 (2)	0.4128 (2)	0.0250 (6)
C6	0.5981 (5)	1.0853 (2)	0.3844 (2)	0.0268 (6)
H6A	0.4539	1.1042	0.3529	0.032*
C7	0.6405 (5)	0.9890 (2)	0.40334 (19)	0.0240 (5)
H7A	0.7868	0.9732	0.4349	0.029*
C8	0.4777 (5)	0.9050 (2)	0.37894 (18)	0.0222 (5)
C9	0.2473 (5)	0.9190 (2)	0.3366 (2)	0.0248 (6)
H9A	0.1911	0.9837	0.3252	0.030*
C10	0.1021 (5)	0.8388 (2)	0.31147 (19)	0.0238 (5)
H10A	−0.0501	0.8491	0.2827	0.029*
C1	0.7028 (5)	1.4507 (2)	0.4124 (2)	0.0301 (6)
H1A	0.7357	1.5184	0.4211	0.036*
C12	0.4120 (5)	0.7255 (2)	0.3732 (2)	0.0259 (6)
H12A	0.4659	0.6607	0.3856	0.031*
C13	0.5557 (5)	0.8070 (2)	0.39794 (19)	0.0238 (5)
H13A	0.7068	0.7965	0.4277	0.029*
C11	0.1866 (5)	0.7422 (2)	0.32979 (19)	0.0224 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0200 (3)	0.0344 (4)	0.0281 (4)	−0.0065 (3)	0.0004 (3)	−0.0013 (3)
Cl1	0.0258 (4)	0.0293 (4)	0.0341 (4)	−0.0077 (3)	0.0020 (3)	−0.0027 (3)
O1	0.0221 (10)	0.0339 (12)	0.0397 (13)	−0.0002 (8)	−0.0060 (9)	0.0006 (9)
C2	0.0217 (13)	0.0321 (15)	0.0342 (16)	0.0004 (11)	0.0034 (11)	−0.0023 (12)
C3	0.0171 (11)	0.0235 (12)	0.0262 (13)	−0.0011 (9)	0.0012 (9)	−0.0021 (10)
C4	0.0174 (11)	0.0281 (13)	0.0207 (12)	−0.0040 (10)	0.0001 (9)	−0.0028 (10)
C5	0.0201 (12)	0.0304 (14)	0.0243 (13)	−0.0007 (10)	0.0014 (10)	−0.0009 (10)
C6	0.0191 (12)	0.0287 (14)	0.0312 (15)	−0.0021 (10)	−0.0029 (10)	0.0005 (11)
C7	0.0172 (11)	0.0281 (13)	0.0262 (13)	−0.0028 (10)	0.0007 (9)	−0.0002 (10)
C8	0.0173 (11)	0.0266 (13)	0.0224 (12)	0.0009 (9)	0.0016 (9)	−0.0015 (10)
C9	0.0170 (12)	0.0288 (14)	0.0279 (14)	0.0025 (10)	−0.0003 (10)	0.0004 (11)
C10	0.0170 (11)	0.0307 (13)	0.0233 (13)	0.0012 (10)	0.0004 (9)	0.0023 (10)
C1	0.0288 (14)	0.0307 (14)	0.0318 (15)	−0.0076 (11)	0.0072 (11)	−0.0024 (12)
C12	0.0224 (13)	0.0252 (13)	0.0300 (14)	0.0007 (10)	0.0031 (10)	0.0038 (11)
C13	0.0171 (11)	0.0279 (13)	0.0263 (13)	0.0024 (10)	0.0018 (9)	0.0036 (10)
C11	0.0196 (12)	0.0256 (13)	0.0227 (13)	−0.0048 (10)	0.0050 (9)	0.0003 (10)

S1—C1	1.691 (3)	C7—C8	1.473 (4)
S1—C4	1.713 (3)	C7—H7A	0.9300
Cl1—C11	1.735 (3)	C8—C9	1.398 (4)
O1—C5	1.224 (3)	C8—C13	1.400 (4)
C2—C1	1.369 (4)	C9—C10	1.377 (4)
C2—C3	1.428 (4)	C9—H9A	0.9300
C2—H2A	0.9300	C10—C11	1.393 (4)
C3—C4	1.397 (4)	C10—H10A	0.9300
C3—H3A	0.9300	C1—H1A	0.9300
C4—C5	1.468 (4)	C12—C11	1.385 (4)
C5—C6	1.474 (4)	C12—C13	1.386 (4)
C6—C7	1.333 (4)	C12—H12A	0.9300
C6—H6A	0.9300	C13—H13A	0.9300
C1—S1—C4	92.14 (14)	C9—C8—C7	122.6 (3)
C1—C2—C3	112.8 (3)	C13—C8—C7	119.1 (2)
C1—C2—H2A	123.6	C10—C9—C8	121.3 (3)
C3—C2—H2A	123.6	C10—C9—H9A	119.4
C4—C3—C2	110.6 (2)	C8—C9—H9A	119.4
C4—C3—H3A	124.7	C9—C10—C11	119.0 (2)
C2—C3—H3A	124.7	C9—C10—H10A	120.5
C3—C4—C5	129.8 (2)	C11—C10—H10A	120.5
C3—C4—S1	111.9 (2)	C2—C1—S1	112.5 (2)
C5—C4—S1	118.2 (2)	C2—C1—H1A	123.7
O1—C5—C4	120.3 (3)	S1—C1—H1A	123.7
O1—C5—C6	122.5 (3)	C11—C12—C13	118.9 (3)
C4—C5—C6	117.2 (2)	C11—C12—H12A	120.6
C7—C6—C5	120.9 (3)	C13—C12—H12A	120.6
C7—C6—H6A	119.5	C12—C13—C8	121.2 (2)
C5—C6—H6A	119.5	C12—C13—H13A	119.4
C6—C7—C8	126.2 (3)	C8—C13—H13A	119.4
C6—C7—H7A	116.9	C12—C11—C10	121.3 (2)
C8—C7—H7A	116.9	C12—C11—Cl1	119.3 (2)
C9—C8—C13	118.3 (3)	C10—C11—Cl1	119.3 (2)
C1—C2—C3—C4	0.0 (4)	C6—C7—C8—C13	175.3 (3)
C2—C3—C4—C5	177.7 (3)	C13—C8—C9—C10	−2.0 (4)
C2—C3—C4—S1	−0.2 (3)	C7—C8—C9—C10	177.5 (3)
C1—S1—C4—C3	0.2 (2)	C8—C9—C10—C11	0.8 (4)
C1—S1—C4—C5	−177.9 (2)	C3—C2—C1—S1	0.2 (3)
C3—C4—C5—O1	−180.0 (3)	C4—S1—C1—C2	−0.2 (3)
S1—C4—C5—O1	−2.3 (4)	C11—C12—C13—C8	−0.6 (4)
C3—C4—C5—C6	0.2 (5)	C9—C8—C13—C12	1.9 (4)
S1—C4—C5—C6	177.9 (2)	C7—C8—C13—C12	−177.6 (3)
O1—C5—C6—C7	10.0 (5)	C13—C12—C11—C10	−0.6 (4)
C4—C5—C6—C7	−170.1 (3)	C13—C12—C11—Cl1	−179.6 (2)
C5—C6—C7—C8	180.0 (3)	C9—C10—C11—C12	0.5 (4)
C6—C7—C8—C9	−4.1 (5)	C9—C10—C11—Cl1	179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1	0.93	2.50	2.825 (4)	101
C13—H13A···O1i	0.93	2.58	3.389 (4)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1	0.93	2.50	2.825 (4)	101
C13—H13A⋯O1i	0.93	2.58	3.389 (4)	145

Symmetry code: (i) .